WO2003040148A1 - A process for the preparation of cefixime via alkyl-or aryl-sulfonates - Google Patents
A process for the preparation of cefixime via alkyl-or aryl-sulfonates Download PDFInfo
- Publication number
- WO2003040148A1 WO2003040148A1 PCT/EP2002/011405 EP0211405W WO03040148A1 WO 2003040148 A1 WO2003040148 A1 WO 2003040148A1 EP 0211405 W EP0211405 W EP 0211405W WO 03040148 A1 WO03040148 A1 WO 03040148A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- cefixime
- salts
- methyl
- aminothiazol
- Prior art date
Links
- XTNITADXTZMAHC-CESQOKLMSA-N C=CC(CC[C@H](C1CCCC(/C(/c2c[s]c(N)n2)=N\OCC(O)=O)=O)C2C1=O)=C2C(O)=O Chemical compound C=CC(CC[C@H](C1CCCC(/C(/c2c[s]c(N)n2)=N\OCC(O)=O)=O)C2C1=O)=C2C(O)=O XTNITADXTZMAHC-CESQOKLMSA-N 0.000 description 1
- KUZHNUSETRQMNR-LPYZZLTCSA-N C=CC(CSC1C2C/C=C/C(/C(/c3c[s]c(N)n3)=N\OCC(O)=O)=O)=C(C(O)=O)N1C2=O Chemical compound C=CC(CSC1C2C/C=C/C(/C(/c3c[s]c(N)n3)=N\OCC(O)=O)=O)=C(C(O)=O)N1C2=O KUZHNUSETRQMNR-LPYZZLTCSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/22—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with radicals containing only hydrogen and carbon atoms, attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Definitions
- the salt of compound (IIA) with a tertiary amine preferably triethylamine, N-methylmorpholine, N-ethyldiisopropylamine, or with an amidine, preferably l,8-diazabicyclo[5.4.0]undec-7-ene (DBU), or with a guanidine, preferably tetramethyl guanidine
- DBU l,8-diazabicyclo[5.4.0]undec-7-ene
- a guanidine preferably tetramethyl guanidine
- the S- mercaptobenzothiazole ester (IIIA) optionally as solvate with N- methylpyrrolidinone, N,N-dimethylformamide or formamide
- O- diethylthiophosphoric ester (IIIB) in an organic solvent selected from a halogenated hydrocarbon such as dichloromethane, an ester such as ethyl acetate or methyl
- Salts (IA) can be obtained either in the anhydrous or in the hydrate form.
- methanesulfonic acid highly pure, crystalline Cefixime methanesulfonate monohydrate is obtained. Hydration water can be almost completely removed by drying under reduced pressure, thus improving the stability of the product.
- Step (c) can be carried out according to any conventional method used in the synthesis of cephalosporins, for example by treatment with an organic base, such as a tertiary amine, or with an inorganic base, such as ammonia, alkali (for example sodium or potassium) carbonates, bicarbonates, hydroxides or phosphates, and subsequent treatment of the resulting salts with conventional acids.
- the reaction solvent can be water, or a mixture of water and alcohols, such as methanol, ethanol, propanol or butanol; ketones, such as acetone or methyl ethyl ketone, or other solvents such as tetrahydrofuran or acetonitrile.
- Cefixime (I) can be obtained in the form of hydrate, preferably trihydrate, of other solvates, or unsolvated.
- MeS0 3 H (76.7 ml) is added to the resulting solution, keeping the temperature between 30° and 35°C. After reacting for 1 hour (HPLC analysis), the mixture is cooled to 2°C, the residue is filtered, washed with ethyl acetate and dried to obtain 124.2 g of Cefixime methanesulfonate monohydrate.
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP02782888A EP1442044A1 (en) | 2001-11-09 | 2002-10-11 | A process for the preparation of cefixime via alkyl-or aryl-sulfonates |
JP2003542194A JP2005508387A (en) | 2001-11-09 | 2002-10-11 | Process for the preparation of cefixime via alkyl- or aryl-sulfonates |
US10/494,700 US20050032771A1 (en) | 2001-11-09 | 2002-10-11 | Process for the preparation of cefixime via alkyl-or aryl-sulfonates |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ITMI2001A002364 | 2001-11-09 | ||
IT2001MI002364A ITMI20012364A1 (en) | 2001-11-09 | 2001-11-09 | SUMMARY PROCESS OF CEFIXIMA VIA ALCHIL-O ARILSOLFONATI |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2003040148A1 true WO2003040148A1 (en) | 2003-05-15 |
Family
ID=11448587
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2002/011405 WO2003040148A1 (en) | 2001-11-09 | 2002-10-11 | A process for the preparation of cefixime via alkyl-or aryl-sulfonates |
Country Status (6)
Country | Link |
---|---|
US (1) | US20050032771A1 (en) |
EP (1) | EP1442044A1 (en) |
JP (1) | JP2005508387A (en) |
KR (1) | KR20050035178A (en) |
IT (1) | ITMI20012364A1 (en) |
WO (1) | WO2003040148A1 (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007013043A2 (en) * | 2005-07-29 | 2007-02-01 | Ranbaxy Laboratories Limited | Processes for the preparation of 7-amino-3-vinyl cephalosporanic acid |
CN103087080A (en) * | 2011-11-03 | 2013-05-08 | 石药集团中奇制药技术(石家庄)有限公司 | Preparation method and synthesis intermediate of cefcapene pivoxil hydrochloride |
CN103833772A (en) * | 2014-02-28 | 2014-06-04 | 广州白云山制药股份有限公司广州白云山化学制药厂 | Method for synthesizing cephalosporin |
CN103965217A (en) * | 2014-05-21 | 2014-08-06 | 广州白云山制药股份有限公司广州白云山化学制药厂 | Preparation method of 3-triazinylcyclo-7-(thiazolylcarboxylmethoxyimino)cephalosporanic acid |
CN104193765A (en) * | 2014-08-12 | 2014-12-10 | 浙江普洛得邦制药有限公司 | Method for synthesizing cefixime |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006067806A1 (en) * | 2004-12-21 | 2006-06-29 | Lupin Limited | Process for the preparation of cefixime |
CN1312158C (en) * | 2005-05-20 | 2007-04-25 | 天津市医药集团技术发展有限公司 | Method for preparing cefixime |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1997024358A1 (en) * | 1995-12-27 | 1997-07-10 | Hanmi Pharmaceutical Co., Ltd. | Process for preparation of cefdinir |
WO1998031685A1 (en) * | 1997-01-16 | 1998-07-23 | Biochemie Gesellschaft Mbh | Purification process |
WO1999051607A2 (en) * | 1998-04-02 | 1999-10-14 | Biochemie Gesellschaft Mbh | Process for purification of a cephalosporin derivative |
WO2001070749A1 (en) * | 2000-03-20 | 2001-09-27 | Hanmi Fine Chemicals Co. Ltd. | A process for preparing cephalosporin derivatives using new thiazole compound |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4260543A (en) * | 1978-07-03 | 1981-04-07 | Merck & Co., Inc. | Crystalline N-formimidoyl thienamycin |
US4748238A (en) * | 1984-03-14 | 1988-05-31 | Merck & Co., Inc. | Crystalline 1R,5S,6S,8R-1-methyl-2-(N,N-dimethylcarbamimidoylmethylthio)-6-(1-hydroxyethyl)-1-carbapen-2-em-3-carboxylic acid |
IE60588B1 (en) * | 1986-07-30 | 1994-07-27 | Sumitomo Pharma | Carbapenem compound in crystalline form, and its production and use |
US4866171A (en) * | 1987-04-11 | 1989-09-12 | Lederle (Japan), Ltd. | (1R,5S,6S)-2-[(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazolium-6-yl)]thio-6-[R-1-hydroxyethyl]-1-methyl-carbapenum-3-carboxylate |
ES2131560T3 (en) * | 1992-11-17 | 1999-08-01 | Sankyo Co | DERIVATIVE OF CRYSTALLINE CARBAPENEM. |
TWI250160B (en) * | 1999-07-06 | 2006-03-01 | Sankyo Co | Crystalline 1-methylcarbapenem compound |
-
2001
- 2001-11-09 IT IT2001MI002364A patent/ITMI20012364A1/en unknown
-
2002
- 2002-10-11 WO PCT/EP2002/011405 patent/WO2003040148A1/en not_active Application Discontinuation
- 2002-10-11 JP JP2003542194A patent/JP2005508387A/en active Pending
- 2002-10-11 EP EP02782888A patent/EP1442044A1/en not_active Withdrawn
- 2002-10-11 US US10/494,700 patent/US20050032771A1/en not_active Abandoned
- 2002-10-11 KR KR1020047006841A patent/KR20050035178A/en not_active Application Discontinuation
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1997024358A1 (en) * | 1995-12-27 | 1997-07-10 | Hanmi Pharmaceutical Co., Ltd. | Process for preparation of cefdinir |
WO1998031685A1 (en) * | 1997-01-16 | 1998-07-23 | Biochemie Gesellschaft Mbh | Purification process |
WO1999051607A2 (en) * | 1998-04-02 | 1999-10-14 | Biochemie Gesellschaft Mbh | Process for purification of a cephalosporin derivative |
WO2001070749A1 (en) * | 2000-03-20 | 2001-09-27 | Hanmi Fine Chemicals Co. Ltd. | A process for preparing cephalosporin derivatives using new thiazole compound |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007013043A2 (en) * | 2005-07-29 | 2007-02-01 | Ranbaxy Laboratories Limited | Processes for the preparation of 7-amino-3-vinyl cephalosporanic acid |
WO2007013043A3 (en) * | 2005-07-29 | 2007-05-31 | Ranbaxy Lab Ltd | Processes for the preparation of 7-amino-3-vinyl cephalosporanic acid |
CN103087080A (en) * | 2011-11-03 | 2013-05-08 | 石药集团中奇制药技术(石家庄)有限公司 | Preparation method and synthesis intermediate of cefcapene pivoxil hydrochloride |
CN103087080B (en) * | 2011-11-03 | 2016-08-31 | 石药集团中奇制药技术(石家庄)有限公司 | The preparation method of a kind of Method of cefcapene pivoxil hydrochloride and synthetic intermediate thereof |
CN103833772A (en) * | 2014-02-28 | 2014-06-04 | 广州白云山制药股份有限公司广州白云山化学制药厂 | Method for synthesizing cephalosporin |
CN103965217A (en) * | 2014-05-21 | 2014-08-06 | 广州白云山制药股份有限公司广州白云山化学制药厂 | Preparation method of 3-triazinylcyclo-7-(thiazolylcarboxylmethoxyimino)cephalosporanic acid |
CN104193765A (en) * | 2014-08-12 | 2014-12-10 | 浙江普洛得邦制药有限公司 | Method for synthesizing cefixime |
CN104193765B (en) * | 2014-08-12 | 2016-08-17 | 浙江普洛得邦制药有限公司 | A kind of synthetic method of cefixime |
Also Published As
Publication number | Publication date |
---|---|
JP2005508387A (en) | 2005-03-31 |
ITMI20012364A1 (en) | 2003-05-09 |
EP1442044A1 (en) | 2004-08-04 |
KR20050035178A (en) | 2005-04-15 |
US20050032771A1 (en) | 2005-02-10 |
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